Active Ester Resin Unsaturated Bonds Heat Resistance

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Solution Overview

Problem

Cured products from existing resin compositions with active ester compounds exhibit low heat resistance despite achieving low dielectric loss tangents, which is a requirement for advanced electronic devices.

Innovation Solution

An active ester resin is developed as a reaction product of a first aromatic compound with two or more phenolic hydroxy groups, a second aromatic compound with a phenolic hydroxy group, and a third aromatic compound with two or more carboxy groups, incorporating an unsaturated bond-containing substituent, which enhances cross-linking density and heat resistance while maintaining low dielectric loss tangent.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Loss of energy

If an active ester compound is used to reduce dielectric loss tangent, then the dielectric loss tangent of the cured product is reduced, but the heat resistance becomes insufficient

Engineering Contradiction:
Improvedielectric loss tangentVSAvoidheat resistance
Core Design Contradiction:
Loss of energyVSTemperature

Solution Approach 1:

The invention changes the chemical structure parameters of the active ester compound by introducing unsaturated bonds (vinyl or allyl groups) at specific positions in the molecular structure. This structural modification enables the compound to achieve both low dielectric loss tangent and high heat resistance simultaneously, resolving the contradiction between these two properties.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention creates a composite curing system by combining the specially structured active ester compound with epoxy resin. The composite material leverages the low dielectric loss properties of the active ester compound while the epoxy resin provides the heat resistance, achieving both desired properties in the cured product.

Inventive Principle:
Principle #40Composite materials

2Reliability

If the resin composition is optimized for low dielectric loss tangent, then the dielectric performance is improved, but the heat resistance deteriorates

Engineering Contradiction:
Improvedielectric performanceVSAvoidheat resistance
Core Design Contradiction:
ReliabilityVSTemperature

Solution Approach 1:

The invention modifies the chemical parameters of the active ester compound by introducing unsaturated bonds at specific positions, which changes the curing characteristics and network structure of the cured product. This enables the material to achieve both excellent dielectric performance and high heat resistance, resolving the contradiction between these two reliability aspects.

Inventive Principle:
Principle #35Parameter changes

Applied Scientific Principles

This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.

Function Achieved in This Case

The active ester resin achieves a balance of low dielectric loss tangent and higher heat resistance in cured products, suitable for applications in semiconductor package substrates and printed circuit boards.

Implementation Method 1

incorporating an unsaturated bond-containing substituent, which enhances cross-linking density and heat resistance

Methodology Applied
Scientific EffectCross-linking: Chemical Bonding

Implementation Method 2

a reaction product of a first aromatic compound having two or more phenolic hydroxy groups, a second aromatic compound having a phenolic hydroxy group, and a third aromatic compound having two or more carboxy groups

Methodology Applied
Scientific EffectEsterification reaction: Chemical Bonding

Data Source

PatentUS11548977B2Active ester resin and composition and cured product using the same
Publication Date: 2023.01.10 DIC CORP
  • US11548977B2 patent drawing
  • US11548977B2 patent drawing
  • US11548977B2 patent drawing

AI summary

The present invention aims to provide a means by which a cured product to be obtained has a low dielectric loss tangent and higher heat resistance. Specifically, provided is an active ester resin that is a reaction product of a first aromatic compound having two or more phenolic hydroxy groups, a second aromatic compound having a phenolic hydroxy group, and a third aromatic compound having two or more carboxy groups and/or an acid halide thereof or an esterified compound thereof, in which at least one of the first aromatic compound, the second aromatic compound, and the third aromatic compound and/or the acid halide thereof or the esterified compound thereof has an unsaturated bond-containing substituent.